EFFICIENT SYNTHESIS OF ALKOXYANTHRAQUINONES FROM FLUOROANTHRAQUINONES AND THEIR PRELIMINARY ELECTROCHEMISTRY

The reaction of 1,8-dichloroanthraquinone with CsF in DMSO under anhydrous conditions affords improved yields of the corresponding difluoro derivative 2. Nucleophilic displacement reactions using simple alkoxide nucleophiles or crown ether derivatives on 2 allows the preparation of 1,8-dialkoxyanthraquinones 5-10 in good to excellent yields. Compounds 8 and 10 exhibit enhanced sodium binding properties upon reduction to the corresponding mono- and dianions. Cation binding enhancements are larger than those previously observed for structurally related systems.